Company: Chesapeake Bay Outward Bound School

Job Type: Full Time

Job Description


Spring Start: March 24th – July 11th Training
Summer Start: July 5th – October 23rd Training


New instructors at Chesapeake Bay Outward Bound School start their employment with a rigorous, training-heavy 16-week period meant to prepare them to become full-time instructors at or before the end of the 16-week period. New instructors will spend the first phase of this period in formal trainings designed to introduce instructors to what it means to work with students, how to manage risk in our course areas, and how to create the outcomes-oriented student experience we strive for. In the second phase, new instructors will begin to engage with our work! New instructors will work primarily in support roles and as co-instructors on programs. Through working in the support role, new instructors gain an inside-look at how our base operates and the work that goes into creating a successful program. While co-instructing on both Day Programs and Expeditions, they will observe and experience what makes an excellent Outward Bound program and apply their training, all with the support of experienced lead instructors. Both program support work and co-instructing provide new instructors with experience and knowledge that will be formative for their career as an instructor. 


A Year at CBOBS

During the Spring and Fall seasons, we partner with nearby public, charter, and independent schools to deliver 5-day peer leadership expeditions. In the Summer, we welcome students from around the world on longer, 8- to 12-day expeditions. We backpack on the Appalachian Trail and in the Dolly Sods Wilderness, canoe on the Potomac River, and sea kayak on the Nanticoke River near the Chesapeake Bay. Similarly, our day programs serve mostly school students during the Spring and Fall. Over the Summer, we work with groups from summer enrichment programs, camps, or mentorship groups. Throughout the year we also run the Police Youth Challenge – a program designed to bring students from Baltimore and Baltimore Police Officers together for a day of building trust and breaking down bias. From mid-November to mid-March, our base shuts down for the Winter months; during this time, instructors often travel, find other work in education or the service industry, and/or pursue other interests in the Baltimore area. 

Chesapeake Bay Outward Bound School’s Baltimore base provides the best of both worlds. Located in the 1,216 acre Gwynns Falls Leakin Park in Baltimore, MD, the base is within city limits, with easy access to Baltimore City while still being in a huge, wooded park.  

Chesapeake Bay Outward Bound School is also actively developing a base in Washington, D.C., with offices located at the Josephine Butler Parks Center. Our D.C. partnerships are growing constantly, and we work directly with D.C. Parks and Recreation in an effort to revitalize several of D.C.’s green spaces. 

If you are motivated to serve young people and be a part of a supportive, fun, and hard-working community, apply to be an Instructor today! 


How to Apply

email [email protected]
Posted on: February 15, 2023
Job Type: Full Time
Job Starting Date:
March 24, 2023
Application Closing Date:
February 29, 2024
Job Salary Range:
Job Activity(ies): Backpacking
Population(s) Served: Youth - Teen
Job Category(ies): Experiential Education
Region(s): US